When do you leave a startup? If you're the CEO, you're kind of obliged to stay at the helm as long as possible, right?

Ranjith Kumaran says that you have to weigh your responsibilities (to funders and employees) against your own skills and interests. "If you feel you have another startup in you, and especially if you are running a successful company, now's the time. Use your founder DNA."

His story: He co-founded the large-file transfer service YouSendIt in 2005. It was a success; by 2010 it had ramped up to over $24 million a year in revenue. Working at this company became a low-risk job, and Kumaran ended up doing M&A. The company was growing nicely and that had a mature management team.

Heaven, right? Not for him. "I like the early-stage stuff," he says. "I love the butterflies in the stomach when I wake up every morning. I want to be that guy."

If you're an entrepreneur, you probably get this.

Kumaran left YouSendIt when it was doing well, he says, so he could start PunchTab (in January of this year), a loyalty platform for Web site owners and bloggers. (No, I don't quite understand that blurb either.) But the point is that he feels he's more effective as a beach-stormer. For sure, we need guys like him. But what do we do with them once the ground is won?

He adds that bailing out of a no-longer-a-startup company that's working is not just about following your passion. You have to time it. He thinks the current easy-money environment has another 18 months of life in it, if that. After that, "it will be worse than 2008." You might end up sitting in a good job after that, but you won't be able to leave it.

This is the last Startup Secret for 2011. I started this daily experiment about two weeks ago, and I'll pick it up again in 2012, after my long winter's nap. If you would like to share a secret, or comment on this series, please drop me a line. Happy holidays!

About the author

Rafe Needleman reviews mobile apps and products for fun, and picks startups apart when he gets bored. He has evaluated thousands of new companies, most of which have since gone out of business.
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